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Starting the game of Survivor, Westman was not immediately targeted. When the game began with all 20 castaways on the same island, it was revealed later in the show that Westman was in an early alliance with Ian Rosenberger, Katie Gallagher and Stephenie LaGrossa. However, when it came time to pick tribes, LaGrossa ended up on Ulong, whereas Westman, Rosenberger, and Gallagher all ended up on Koror. The alliance between Westman, Rosenberger, and Gallagher stayed strong on Koror, despite the loss of LaGrossa.

Originally planning to hide behind the younger males of his tribe, Westman soon became known for leadership skills. Koror team-members secured early immunity wins in Episodes 1-4. Westman, Rosenberger, and Gallagher joined together with Gregg Carey and Jenn Lyon to control the numbers on Koror. In Episode 5, both tribes faced tribal council regardless of the challenge outcome, and Tom joined the rest of his tribe to vote out tribal annoyance Willard Smith.

In Episode 7, Westman caught a shark for his tribe. Ulong continued to suffer until only LaGrossa remained. She joined Koror in Episode 9 in an unofficial merge. Together with LaGrossa, Westman's alliance controlled the game and voted out Coby Archa.

At the Final 8, Westman's allies Carey and Lyon decided to vote out LaGrossa, despite Westman's campaigning for her. But Janu Tornell unexpectedly quit the game at tribal council after LaGrossa broke down once. At the Final 7, LaGrossa tried to organize an alliance of women against Westman, but Caryn Groedel would not commit and informed Westman of the plan, leading to LaGrossa being unanimously voted out.

At the Final 6, Westman was comfortable with his immunity wins and his alliance. However, he received a shock when Rosenberger informed him that Carey and Lyon had swayed Gallagher to their side to turn on Westman at the Final 5. When Carey, Lyon and Gallagher were enjoying a reward, Tom, Ian and Caryn conspired to get rid of Carey instead. They even contemplating drawing rocks in random elimination. But it never came to that stage as Rosenberger informed Gallagher of the plan minutes before tribal council and she had no choice but to comply or risk elimination by random rock drawing, and Carey was voted out.

At the Final Five, the alliance of Westman, Rosenberger and Gallagher were on shaky ground due to the betrayal of Westman and Rosenberger instigating Carey's departure. Gallagher and Lyon agreed to team up with Caryn to control the game. This was further pushed when Rosenberger took Westman on a reward, despite promising to take Gallagher. This angered Gallagher and led to an argument with Rosenberger after he returned. But after the two reconciled, they agreed to get rid of Caryn instead, abandoning the all-female alliance. At the Final Four, Rosenberger contemplated turning on Westman and siding with Gallagher and Lyon to vote off Westman. But when Westman enjoyed another immunity win, Rosenberger agreed that Lyon would be the next to go. However, when Westman found out about Rosenberger's plan, he sided with Lyon and voted for Rosenberger. But Gallagher stayed true to Rosenberger, resulting in a 2-2 tie. Both Rosenberger and Lyon participated in a fire-building tie-breaker competition. Rosenberger won, and Lyon was voted out.

At the Final 3, heavy arguments took place, especially between Rosenberger and Westman. Rosenberger felt as if he had betrayed his friends, and protested that he did not come to play the role of the villain. In the endurance immunity challenge, after close to 12 hours, Rosenberger agreed to step down and be voted off in a sign of repentance for betraying Westman and Gallagher. Westman accepted and Rosenberger was voted out. This immunity win was Tom's fifth out of only seven individual immunity challenges, a feat matched only by Colby Donaldson(Survivor: The Australian Outback), Terry Deitz(Survivor: Panama), and Oscar "Ozzy" Lusth(Survivor: Cook Islands) who won five out of only six individual immunity challenges.

In the end, Westman defeated Gallagher in a 6-1 vote to become the Sole Survivor. He managed to gain the votes of Tornell, LaGrossa, Carey, Groedel, Lyon and Rosenberger.

Westman participated on the Heroes tribe. He had discovered several chickens on Day 1, which all of his tribe was able to surround and catch. At the beginning of the game, he made an alliance with Colby Donaldson and Stephenie LaGrossa. The tribe beat the villains at the first reward challenge, but lost at immunity. On Day 3, Westman and the rest of the tribe voted out Jessica Kiper because of her emotions and her weakness. After going to tribal council a second time, Tom was one of only three people who attempted to vote out Amanda Kimmel, but failed to do so when fellow Survivor: Palau contestant Stephenie LaGrossa was voted out. Tom found the hidden immunity idol at the Heroes campsite and got a target on his back. At the fourth (third for the Heroes) tribal council, Tom played the idol which negated three votes cast against him which ended up sending Cirie Fields home. After James Clement had injured his leg at the following reward challenge, Westman attempted to ensure the elimination of Clement. After losing their fourth immunity challenge, Westman attempted to vote out Amanda, however the Heroes tribe elected to keep Kimmel and Clement over Westman, and he was voted out 5-2. He played Survivor for a combined total of 53 days.